Iterative Assembly of Macrocyclic Lactones using Successive Ring Expansion Reactions

Chemistry : a European Journal
Thomas C StephensWilliam P Unsworth

Abstract

Macrocyclic lactones can be prepared from lactams and hydroxyacid derivatives via an efficient 3- or 4-atom iterative ring expansion protocol. The products can also be expanded using amino acid-based linear fragments, meaning that macrocycles with precise sequences of hydroxy- and amino acids can be assembled in high yields by "growing" them from smaller rings, using a simple procedure in which high dilution is not required. The method should significantly expedite the practical synthesis of diverse nitrogen containing macrolide frameworks.

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Citations

Oct 10, 2019·Macromolecular Rapid Communications·Yang LiangZi-Long Li
Sep 14, 2019·Chemistry : a European Journal·Stefan ZimmermannKamal Kumar
Jan 26, 2021·Organic & Biomolecular Chemistry·Kleopas Y PalateWilliam P Unsworth
Mar 2, 2020·Chemical Science·Aimee K Clarke, William P Unsworth
Jul 3, 2021·Angewandte Chemie·Guillaume ForceDavid Lebœuf
May 29, 2020·Organic Letters·Sadegh Shabani, Craig A Hutton

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Methods Mentioned

BETA
column chromatography

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